Gilt Groupe's Alexis Maybank: The Woman Behind The $1 Billion Company

Most people couldn't pull off the feat of leaving a stable career to pursue a passion and develop it into a $1 billion company. But that's the experience of Alexis Maybank, the founder and chief strategy officer of Gilt Groupe Inc., the members-only online shopping website.

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Founded five years ago by Maybank, along with her close friend Alexandra Wilkis Wilson and three others, Gilt.com is "one of the most addictive websites that exist today," according to Mashable.com, the online digital news website. With 5 million customers, Gilt.com offers luxury products for discounts of up to 70 percent off.

To those who know Maybank, 37, and have worked with her since the launch of Gilt.com, the success came as little surprise. She is described as a fashion-lover who also is tough and determined.

"You would expect to see her at high-end New York restaurants, looking fashionable," says Nick Beim, one of Gilt.com's original investors. (Beim is the general partner of Matrix Partners, a New York-based venture capital firm.) "But she also has a serious outdoors side to her. You don't spend months at a time camping on glaciers in Alaska unless you have some very serious steely" resolve.

Her grittiness was also on display during the launch of Gilt.com, which took place five years ago, in Nov. 2007. According to Wilson, her partner, Maybank's initial title of CEO didn't stop her from working shifts in the storage warehouse or handling calls from customers about problems they were having with their orders.

Her love of fashion doesn't fall into the straight-and-narrow, either, according to Wilson, her partner. She says Maybank's favorite designers include Dolce and Gabbana and Alexander McQueen. "She has fun with fashion, it just doesn't just have to be classic," Wilson says, and adds that her partner's "confidence," is also evident in her comfort in high-heel shoes, or her occasional sporting of leopard print.

Gilt.com grew out of Maybank and Wilson's shared passion for New York City sample sales -- where it's possible for customers to buy designer fashion at steep discounts. Maybank, then working on Wall Street, and Wilson, an exec in the corporate office of a fashion company, often would sneak off to go to "sample sales where we could shop and find little treasures," Wilson told the Jewish United Fund in an online interview.

Then they had a big idea: why not export the typical New York-event to the Internet? (Maybank also was once an employee of AOL, working as a general manager of the company's commerce business.)

So in 2007, Gilt.com was born. There's little doubt the business has struck a chord with avid shoppers.

"People tag me by the sleeve and tell me it's changed their lives," Susan Lyne, the chairman of Gilt Groupe, told the Daily Beast. "They tell me their stories of how at 12:01 p.m," which is when the new sales are presented to members. "Every day life just stops for them. It's like a religion, that deep. I've never seen anything like this."

Five years into launching their business, the company was valued last summer at just over $1 billion and counts 900 employees. Along the way, Maybank has found time to start a family, and now has two children. She also published a book in April, a New York Times bestseller, "By Invitation Only."

Maybank encourages everyone, especially women, to take big risks in their careers. But she stresses the importance of making responsible choices.

"It's worse to wonder what-if," she told Draper, but also added: "Think about, 'If I left what I was doing today, and what idea I was pursuing didn't work out? What would happen then? Could I go back to that old job?' Often, the answer is yes, or something substantially similar."

In Maybank's case, Gilt represented a continuation of sorts. After attending Harvard, where she met Wilson, Maybank became one of the earliest employees of eBay, where she helped found eBay motors.

It was at eBay, she told Draper, that she learned the power of "word-of-mouth," in launching an online business, a model that she said has also been vital in Gilt's success.